‘Taking time can bring amazing results’

As told to Nicole Swengley

Sean Caulfield, 40, grew up in Essex, eastern England. He left school at 16, worked in various retail businesses until he was 30 and then moved to Italy, where he set up and runs To Tuscany, a property rental company. He lives in Chianti.

I was born in Dagenham, Essex, and grew up in Gidea Park, Romford. My Irish father had moved to England and by the time I was growing up he was chief executive of International Stores, one of the biggest supermarket chains at that time. This really gave me the confidence to set out to achieve whatever I wanted. It also helped to live in a neighbourhood where all the people around me started with very little yet created hugely successful businesses. So, in a way, setting up a company came naturally to me.

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I always knew I would have my own company and was excited by the retail world because I felt free to express my ideas and got a real thrill when they were successful. By the time I was 18 I was manager of a small supermarket. Then my father set up a chain of confectionery stores and invited me to be part of the business.

My passion for all things Italian was sparked by meeting my Italian wife, Sabina. She had moved to Britain to learn English and was working in a hotel in Canterbury, Kent, when we met. I lived in that area for nine years and spent most of my 20s building a flowers and plants distribution service that became a national company. During this period of intense work I started travelling to Italy with Sabina and discovered a new world. I had always thought of Italy with all the clichés attached – mafia, football, pasta and wine – but I was blown away by the diversity of cultures I found and wanted to know more.

On the first trip to Sabina’s parents’ farm I arrived at night. It was Christmas-time. As I drove through the valleys I could see the silhouette of high mountains all draped with wonderful Christmas stars. When dawn broke it revealed the amazing Alpine valleys. I was in a small market town called Prato allo Stevio, the home town of my wife’s family, halfway up the Val Venosta in the Alpine mountain region of Trentino-Alto Adige. I was immediately drawn to the varying landscapes of the lush valley from a glacier at the top to strawberry fields and vines below. Now famous for its apple production, the valley floor was then mainly given over to dairy farming.

Prato allo Stevio is not often visited by English people so the locals didn’t know how to take me. They are used to tourists from all over Italy but an Englishman who was part of the furniture was something different altogether.

I lived and worked on my in-laws’ dairy farm, which is 20 minutes from the ski resort of Solda. This was ideal for me as I have always been a keen skier. I spent much of my time discovering the Dolomites, including Europe’s largest linked skiing area, the Dolomiti Super-ski. I loved exploring the mountains – ski touring, hiking and downhill skiing – and the hospitality was second to none. I also loved the fact that Alto Adige has a dual culture of Germanic and Italian influences in all aspects of daily life from design to cuisine. With the cuisine, for example, they manage to take the best from both cultures and blend them to create extraordinary results. Main courses tend to be Italian creations with local smoked meats, salamis, cheese and pasta, while desserts, cakes and breads come under the Austrian influence.

I’d always thought I could manage any type of work but quickly realised that I wasn’t born to be a farmer. I loved being in the mountains and felt privileged to have the opportunity to be part of day-to-day life there but I knew that this was not the way I wanted to do it. My love of the mountains took me to Val d’Aosta, where I initially considered setting up a ski website. Once again, I loved the dual influences of the two different cultures – this time Franco-Italian – and of course found the skiing to be fantastic. At the top of Val d’Aosta is Courmayeur, an affluent town where the skiing is limited but style is everything. Apres-ski is sipping a Campari in your designer ski-suit!

One of my first goals was to learn the Italian language and speak it like a native. Siena is the best place in Italy for a foreigner to learn Italian as there is virtually no local dialect. I looked up an old friend who lived near the city and she helped me get started.

It was love at first sight. I was overwhelmed by the region’s natural beauty, the warmth of the people and how they treasure their way of life. I had heard what a beautiful city Siena is but was taken aback by the architecture and friendliness of its people. There is also minimal crime due to family ties, traditional values and the prominence given to its art and history.

Most of all, I really got the sense that everyone is given the space to be who they want in this part of Italy. I felt liberated. And the countryside surrounding Siena was the most beautiful I had ever experienced. The rolling hills of the Chianti, in all their diversity, still move me on a daily basis.

Setting up my property rental company, however, proved extremely difficult, complicated and frustrating. The first lesson I learned was to forget how it would be done in Britain and get local help to learn how it has to be done in Italy. You find yourself saying: “We don’t do it like this in the UK”. But you have to stop right there and remember that it really doesn’t matter to the Italians how we do things in Britain.

You have to take baby steps to begin with and understand that there are no shortcuts. Each move takes a long time – longer than you ever imagined – but it’s worth it. The red tape comes as part of the whole deal. Did you know, for example, that you need a chemistry degree before you have the right to employ a cleaner? It’s something to do with having full knowledge about cleaning fluids.

Business-wise, it has been a real learning curve for me. The business culture is so much more about personalities and relationships than in Britain. I had to learn to do things differently and at a different pace. I think the speed at which everything was done was the biggest problem. At the pace I was used to moving in Britain I could have set up a number of national companies and still had time to set up a few clubs and bars around the country. It was a real challenge to learn how to do things at a more leisurely pace but, in the end, I’m very glad I did it.

Culturally, it was more of an adventure than a learning curve. I was instantly hit by wonder and excitement when I first visited my wife’s family home and saw the endless possibilities that the landscape alone presented to its inhabitants.

I absolutely adore everything about Italy – the food, the people, the way that two cultures can seamlessly join and present new and wonderful things to experience. The only thing that could be better is the speed at which things are done. Still, I’m coming round to the fact that taking your time can bring amazing results. And the only things I really miss about Britain are PG Tips tea, a good pint of Guinness and the cricket.